Crystal structure of di-cyclo-hexyl-ammonium nitrate(V).

In the title mol-ecular salt, C12H24N(+)·NO3 (-), the cyclohexyl rings adopt chair conformations with the exocyclic C-N bonds in equatorial orientations. In the crystal, a bifurcated N-H⋯(O,O) hydrogen bond links the cation to the anion; the ion pairs are linked via C-H⋯O hydrogen bonds, forming layers in the ac plane.

Related literature

For the crystal structure of di­cyclo­hexyl­ammonium nitrate(III), see: Golobič et al. (1999 ▸). For other crystal structures of di­cyclo­hexyl­ammonium salts, see: Ng (1995 ▸); Bi et al. (2002 ▸); Lo & Ng (2008 ▸); Khawar Rauf et al. (2008 ▸); Selvakumaran et al. (2011 ▸); Ndoye et al. (2014 ▸). For crystal structures of carboxyl­ate salts with the di­cyclo­hexyl­ammonium cation belonging to the low mol­ecular weight gelators (LMWGs) class of compounds and exhibiting gelling properties, see: Trivedi et al. (2004 ▸, 2005 ▸); Sahoo & Dastidar (2012 ▸); Rojek et al. (2015 ▸).

Experimental

Crystal data

C12H24N+·NO3 −

M = 244.33

Orthorhombic,

a = 8.436 (2) Å

b = 18.682 (5) Å

c = 8.427 (3) Å

V = 1328.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.45 × 0.41 × 0.36 mm

Data collection

Kuma KM-4 difractometer with a CCD camera diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▸) T min = 0.962, T max = 0.969

9001 measured reflections

1759 independent reflections

1699 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.089

S = 1.09

1759 reflections

162 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: DIAMOND (Brandenburg, 1999 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015019386/su5222sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019386/su5222Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015019386/su5222Isup3.txt

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015019386/su5222Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015019386/su5222fig1.tif

The asymmetric unit of the title mol­ecular salt, showing the atom-numbering scheme and the symmetry-independent hydrogen bonds (orange and light-blue dashed lines; see Table 1). Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b ac . DOI: 10.1107/S2056989015019386/su5222fig2.tif

A view along the b axis of the crystal packing of the title mol­ecular salt, showing the hydrogen-bonded chains assembled into a layer in the ac plane. Hydrogen bonds are drawn as yellow and light-blue dashed lines (see Table 1). H atoms on C atoms of the cyclo­hexane rings not involved in hydrogen bonds have been omitted for clarity.

CCDC reference: 1431025

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H24N+·NO3−	F(000) = 536
Mr = 244.33	Dx = 1.222 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6847 reflections
a = 8.436 (2) Å	θ = 3–29°
b = 18.682 (5) Å	µ = 0.09 mm−1
c = 8.427 (3) Å	T = 100 K
V = 1328.1 (7) Å3	Block, colorless
Z = 4	0.45 × 0.41 × 0.36 mm

Kuma KM-4 difractometer with a CCD camera diffractometer	1699 reflections with I > 2σ(I)
Radiation source: normal focus sealed tube	Rint = 0.035
ω scans	θmax = 28.7°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −9→11
Tmin = 0.962, Tmax = 0.969	k = −24→22
9001 measured reflections	l = −11→11
1759 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.051P)2 + 0.1971P] where P = (Fo2 + 2Fc2)/3
1759 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.67955 (15)	0.52358 (7)	0.34329 (17)	0.0172 (3)
H1N	0.575 (3)	0.5334 (10)	0.348 (3)	0.022 (5)*
H2N	0.703 (2)	0.5150 (11)	0.245 (3)	0.020 (5)*
C11	0.76844 (18)	0.58933 (8)	0.39662 (19)	0.0174 (3)
H11	0.8844	0.5812	0.3802	0.021*
C21	0.7391 (2)	0.60372 (9)	0.5718 (2)	0.0209 (3)
H21A	0.7773	0.5626	0.6354	0.025*
H21B	0.6239	0.6091	0.5909	0.025*
C31	0.8252 (2)	0.67195 (8)	0.6241 (2)	0.0236 (3)
H31A	0.7994	0.6822	0.7365	0.028*
H31B	0.9411	0.6644	0.6163	0.028*
C41	0.7782 (2)	0.73593 (8)	0.5221 (2)	0.0249 (3)
H41A	0.8415	0.7782	0.5537	0.030*
H41B	0.6649	0.7472	0.5400	0.030*
C51	0.8053 (2)	0.72023 (9)	0.3456 (2)	0.0256 (3)
H51A	0.7681	0.7613	0.2815	0.031*
H51B	0.9202	0.7140	0.3256	0.031*
C61	0.71676 (19)	0.65265 (8)	0.2950 (2)	0.0213 (3)
H61A	0.6012	0.6602	0.3068	0.026*
H61B	0.7390	0.6424	0.1820	0.026*
C12	0.71252 (17)	0.45456 (8)	0.4304 (2)	0.0173 (3)
H12	0.6777	0.4601	0.5432	0.021*
C22	0.61395 (18)	0.39582 (8)	0.3534 (2)	0.0202 (3)
H22A	0.6447	0.3906	0.2406	0.024*
H22B	0.5003	0.4089	0.3575	0.024*
C32	0.64019 (18)	0.32501 (8)	0.4401 (2)	0.0224 (3)
H32A	0.6010	0.3291	0.5504	0.027*
H32B	0.5791	0.2867	0.3866	0.027*
C42	0.81560 (18)	0.30512 (8)	0.4419 (2)	0.0225 (3)
H42A	0.8304	0.2606	0.5040	0.027*
H42B	0.8517	0.2958	0.3320	0.027*
C52	0.91573 (19)	0.36473 (8)	0.5142 (2)	0.0231 (3)
H52A	1.0292	0.3516	0.5073	0.028*
H52B	0.8882	0.3701	0.6278	0.028*
C62	0.88884 (18)	0.43628 (8)	0.4286 (2)	0.0206 (3)
H62A	0.9496	0.4746	0.4822	0.025*
H62B	0.9266	0.4327	0.3176	0.025*
N2	0.27878 (15)	0.55034 (7)	0.44418 (19)	0.0209 (3)
O1	0.15367 (14)	0.57836 (7)	0.48831 (17)	0.0325 (3)
O2	0.33397 (19)	0.49638 (8)	0.51433 (18)	0.0398 (4)
O3	0.35579 (15)	0.57519 (7)	0.32934 (17)	0.0318 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0173 (6)	0.0172 (6)	0.0172 (7)	0.0010 (5)	−0.0018 (5)	−0.0027 (5)
C11	0.0183 (7)	0.0165 (7)	0.0176 (7)	0.0002 (5)	−0.0001 (6)	−0.0019 (5)
C21	0.0260 (7)	0.0202 (7)	0.0165 (7)	−0.0022 (6)	−0.0009 (6)	−0.0014 (6)
C31	0.0288 (8)	0.0199 (7)	0.0220 (8)	0.0000 (6)	−0.0035 (6)	−0.0047 (6)
C41	0.0274 (8)	0.0179 (7)	0.0293 (8)	0.0012 (6)	−0.0015 (7)	−0.0026 (7)
C51	0.0314 (8)	0.0209 (7)	0.0245 (8)	−0.0029 (6)	0.0017 (7)	0.0025 (7)
C61	0.0256 (8)	0.0199 (7)	0.0184 (7)	0.0001 (6)	−0.0003 (6)	0.0021 (6)
C12	0.0170 (6)	0.0162 (6)	0.0187 (7)	0.0009 (5)	−0.0004 (6)	−0.0003 (6)
C22	0.0173 (7)	0.0189 (7)	0.0242 (8)	−0.0007 (5)	−0.0013 (6)	−0.0025 (6)
C32	0.0225 (7)	0.0187 (7)	0.0261 (8)	−0.0011 (5)	0.0034 (7)	−0.0007 (6)
C42	0.0236 (7)	0.0188 (7)	0.0252 (8)	0.0017 (6)	0.0029 (7)	−0.0004 (7)
C52	0.0212 (7)	0.0227 (7)	0.0253 (7)	0.0033 (6)	−0.0045 (6)	0.0005 (7)
C62	0.0178 (7)	0.0196 (7)	0.0243 (8)	0.0002 (5)	−0.0031 (6)	−0.0009 (6)
N2	0.0202 (6)	0.0229 (6)	0.0197 (6)	−0.0009 (5)	−0.0012 (5)	−0.0013 (5)
O1	0.0197 (6)	0.0370 (7)	0.0409 (8)	0.0041 (5)	0.0034 (5)	−0.0079 (6)
O2	0.0594 (9)	0.0360 (7)	0.0239 (6)	0.0236 (6)	0.0088 (7)	0.0071 (6)
O3	0.0296 (6)	0.0394 (7)	0.0263 (7)	0.0000 (5)	0.0050 (5)	0.0082 (6)

N1—C11	1.5077 (19)	C12—C22	1.522 (2)
N1—C12	1.510 (2)	C12—C62	1.526 (2)
N1—H1N	0.91 (2)	C12—H12	1.0000
N1—H2N	0.86 (2)	C22—C32	1.527 (2)
C11—C21	1.521 (2)	C22—H22A	0.9900
C11—C61	1.524 (2)	C22—H22B	0.9900
C11—H11	1.0000	C32—C42	1.526 (2)
C21—C31	1.532 (2)	C32—H32A	0.9900
C21—H21A	0.9900	C32—H32B	0.9900
C21—H21B	0.9900	C42—C52	1.525 (2)
C31—C41	1.525 (2)	C42—H42A	0.9900
C31—H31A	0.9900	C42—H42B	0.9900
C31—H31B	0.9900	C52—C62	1.536 (2)
C41—C51	1.533 (3)	C52—H52A	0.9900
C41—H41A	0.9900	C52—H52B	0.9900
C41—H41B	0.9900	C62—H62A	0.9900
C51—C61	1.528 (2)	C62—H62B	0.9900
C51—H51A	0.9900	N2—O1	1.2353 (18)
C51—H51B	0.9900	N2—O3	1.255 (2)
C61—H61A	0.9900	N2—O2	1.258 (2)
C61—H61B	0.9900
C11—N1—C12	117.34 (12)	H61A—C61—H61B	108.1
C11—N1—H1N	107.9 (13)	N1—C12—C22	107.92 (12)
C12—N1—H1N	109.3 (13)	N1—C12—C62	111.45 (12)
C11—N1—H2N	109.0 (14)	C22—C12—C62	111.51 (12)
C12—N1—H2N	105.4 (14)	N1—C12—H12	108.6
H1N—N1—H2N	108 (2)	C22—C12—H12	108.6
N1—C11—C21	110.62 (13)	C62—C12—H12	108.6
N1—C11—C61	108.83 (13)	C12—C22—C32	109.96 (13)
C21—C11—C61	111.20 (13)	C12—C22—H22A	109.7
N1—C11—H11	108.7	C32—C22—H22A	109.7
C21—C11—H11	108.7	C12—C22—H22B	109.7
C61—C11—H11	108.7	C32—C22—H22B	109.7
C11—C21—C31	110.42 (14)	H22A—C22—H22B	108.2
C11—C21—H21A	109.6	C42—C32—C22	110.87 (13)
C31—C21—H21A	109.6	C42—C32—H32A	109.5
C11—C21—H21B	109.6	C22—C32—H32A	109.5
C31—C21—H21B	109.6	C42—C32—H32B	109.5
H21A—C21—H21B	108.1	C22—C32—H32B	109.5
C41—C31—C21	111.49 (14)	H32A—C32—H32B	108.1
C41—C31—H31A	109.3	C52—C42—C32	111.30 (13)
C21—C31—H31A	109.3	C52—C42—H42A	109.4
C41—C31—H31B	109.3	C32—C42—H42A	109.4
C21—C31—H31B	109.3	C52—C42—H42B	109.4
H31A—C31—H31B	108.0	C32—C42—H42B	109.4
C31—C41—C51	110.99 (13)	H42A—C42—H42B	108.0
C31—C41—H41A	109.4	C42—C52—C62	111.46 (14)
C51—C41—H41A	109.4	C42—C52—H52A	109.3
C31—C41—H41B	109.4	C62—C52—H52A	109.3
C51—C41—H41B	109.4	C42—C52—H52B	109.3
H41A—C41—H41B	108.0	C62—C52—H52B	109.3
C61—C51—C41	110.81 (14)	H52A—C52—H52B	108.0
C61—C51—H51A	109.5	C12—C62—C52	109.50 (13)
C41—C51—H51A	109.5	C12—C62—H62A	109.8
C61—C51—H51B	109.5	C52—C62—H62A	109.8
C41—C51—H51B	109.5	C12—C62—H62B	109.8
H51A—C51—H51B	108.1	C52—C62—H62B	109.8
C11—C61—C51	110.18 (13)	H62A—C62—H62B	108.2
C11—C61—H61A	109.6	O1—N2—O3	121.19 (15)
C51—C61—H61A	109.6	O1—N2—O2	120.95 (16)
C11—C61—H61B	109.6	O3—N2—O2	117.86 (14)
C51—C61—H61B	109.6
C12—N1—C11—C21	−56.99 (17)	C11—N1—C12—C22	−178.34 (13)
C12—N1—C11—C61	−179.43 (13)	C11—N1—C12—C62	−55.58 (18)
N1—C11—C21—C31	−178.14 (13)	N1—C12—C22—C32	−178.66 (12)
C61—C11—C21—C31	−57.10 (18)	C62—C12—C22—C32	58.62 (18)
C11—C21—C31—C41	55.47 (18)	C12—C22—C32—C42	−56.86 (18)
C21—C31—C41—C51	−55.0 (2)	C22—C32—C42—C52	55.7 (2)
C31—C41—C51—C61	55.81 (19)	C32—C42—C52—C62	−55.4 (2)
N1—C11—C61—C51	−179.74 (13)	N1—C12—C62—C52	−178.37 (13)
C21—C11—C61—C51	58.16 (18)	C22—C12—C62—C52	−57.70 (18)
C41—C51—C61—C11	−57.12 (18)	C42—C52—C62—C12	55.69 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.91 (2)	2.56 (2)	3.292 (2)	138.2 (17)
N1—H1N···O3	0.91 (2)	2.01 (2)	2.8988 (19)	166.7 (19)
N1—H2N···O2i	0.86 (2)	1.98 (2)	2.799 (2)	157.6 (19)
C11—H11···O1ii	1.00	2.45	3.347 (2)	149
C12—H12···O3iii	1.00	2.52	3.456 (3)	156
C22—H22B···O2	0.99	2.53	3.309 (2)	136
C62—H62A···O1ii	0.99	2.59	3.506 (2)	153

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NO2	0.91(2)	2.56(2)	3.292(2)	138.2(17)
N1H1NO3	0.91(2)	2.01(2)	2.8988(19)	166.7(19)
N1H2NO2i	0.86(2)	1.98(2)	2.799(2)	157.6(19)
C11H11O1ii	1.00	2.45	3.347(2)	149
C12H12O3iii	1.00	2.52	3.456(3)	156
C22H22BO2	0.99	2.53	3.309(2)	136
C62H62AO1ii	0.99	2.59	3.506(2)	153

Symmetry codes: (i) ; (ii) ; (iii) .